Customer Support Leaders

Send us Fan Mail When a customer asks a “simple question”, your org chart doesn’t matter. What they feel is speed, clarity, and whether they’re being helped or being handed off. That’s why we sat down with Ulrike Pitschke again, now leading Customer Success at Staffbase, to get honest about the real seam between customer support and customer success and how to make it stronger as a SaaS company sc...

Send us Fan Mail Your support queue will always be there tomorrow, so “I’ll automate when things calm down” quietly becomes “never.” Charlotte Ward sits down with Brian Levine to get brutally practical about finding time for automation and using today’s AI tools without turning your job into a second full-time job. We talk about why the barrier to building support workflows has dropped so fast, an...

Send us Fan Mail AI is moving so fast that it’s not just improving customer support, it’s changing what “support software” even is. We sit down with Andrei Kamarouski to unpack the real shift from the pre generative AI era, when teams spent months collecting data and training narrow models, to today’s world where language-first AI can classify tickets, analyse conversations, and accelerate product...

Send us Fan Mail Support teams don’t burn out only because the queue is busy. They burn out when the work feels endless, the career path feels foggy, and “helpful” side requests turn into untracked shadow ops that swallow the day. Charlotte Ward and Alec Moloney dig into what it takes to make customer support a final destination: a place where talented people build long, healthy careers and feel r...

Send us Fan Mail You can change careers without throwing away everything you’ve built, but only if you can explain what you’re carrying with you. We sit down with Cynthia Ng, whose path runs from secondary school teaching to being a technology librarian, then into remote customer support at GitLab, and later into strategy and operations. Along the way, she’s had to translate her experience across...

Send us Fan Mail Support still gets treated like the lobby, not the building. If you’ve ever heard “So what do you want to do after support?” this conversation is for you. Charlotte Ward sits down with Alec Moloney to unpack “support as a final destination” and why perception is the first battleground. We talk about the hangover from call centre era thinking, the stubborn myth that great support p...

Send us Fan Mail You can feel the ground shifting in customer support right now: AI is giving non-technical leaders the ability to build. I sit down with Italo Belandria, Head of Customers at Ringover, to unpack what that actually looks like day to day when you are responsible for customer success and customer support operations but you are not an engineer. We talk about moving beyond “AI writes e...

Send us Fan Mail You’re going to die, and pretending otherwise is a terrible project plan. Val Turner joins us with a blunt premise and then makes it surprisingly hopeful: if you accept the timeline, you can design better defaults for your family, your future self, and even your team at work. We start with Val’s path from customer support into product leadership and the constant translation work i...

Send us Fan Mail “Escalate to engineering” sounds normal, but it quietly shapes how your whole company treats support. We challenge that default and replace it with a more accurate model: routing work to the right skill set, while keeping escalation for the moments that truly need higher priority and attention. Along the way, we explore how small language choices change ownership, expectations, an...

Send us Fan Mail Chaos in customer support rarely starts as chaos. It starts as “organic” growth, a few heroic workarounds, a helpful engineer jumping into Zendesk, or a fast acquisition that bolts on a new product and a new team without a shared operating system. Then the outcomes get unpredictable: escalations drag, customers hear different answers, and everyone feels busy while nothing feels st...

Send us Fan Mail Servant leadership gets talked about a lot, but it’s often treated like a vague “be nice to people” slogan. We take a sharper angle: servant leadership in customer support is competence plus care. That means knowing what you’re doing and genuinely caring about your team, then using both to remove obstacles so they can do their best work. Along the way, we explore why this approach...

Send us Fan Mail Trust doesn’t magically appear because you got the title, and it definitely doesn’t return because you delivered one heroic win. When a customer support team has been burned by toxic management, constant escalations, broken processes, or a product that keeps letting customers down, “prove it” becomes the default setting. We dig into what it means to lead from that reality and how...

Send us Fan Mail AI can make customer support faster, cheaper, and more consistent, but it can also quietly destroy trust when it becomes a wall between customers and real help. Charlotte Ward sits down with customer experience expert Shep Hyken to get brutally clear on what never changes: customers want to be happy, they want you to take care of them, they want it to be easy, and when something b...

Send us Fan Mail Great support can look “perfect” on paper and still fail the customer in real life. That tension is what we dig into with Carl Lenocker, a senior customer success executive, executive coach, and longtime support leader, as we unpack a simple idea with big consequences: outcomes over optics. We get concrete about how traditional support KPIs like first contact resolution, time to a...

Send us Fan Mail Support teams don’t usually fail because they “don’t care” or “aren’t working hard enough.” They fail because they scale on instinct, accumulate tribal knowledge, and measure whatever is easiest until the whole system starts to wobble. We sit down with Neal Travis, Head of Customer Experience and Operations at AIHR, to talk about measuring support maturity in a way that leads to r...

Send us Fan Mail Your one-on-ones shouldn’t feel like a weekly status treadmill where we do all the talking and our team does all the nodding. Charlotte Ward sits down with Greg Skirving to unpack a deceptively simple leadership shift: the reverse one-on-one, where the direct report leads with their perspective instead of waiting for the manager’s agenda.  Greg walks us through his practical struc...

Send us Fan Mail Mary Poppins is “practically perfect” and that makes her a surprisingly useful guide for modern customer support leadership. We (Charlotte Ward and Jason Yun, Head of Provider Success at Prax Health) use the film’s songs and characters to translate timeless ideas into practical support team lessons: hire for kindness and wit, stay close to the frontline, and remember that people a...

Send us Fan Mail Most coaching goes wrong before the coaching conversation even starts. If we only review a tiny sample of calls, chats, or tickets, we end up “coaching the seventh hole” and missing the real issue that shows up earlier in the customer journey, like unclear expectation setting or a pattern that repeats across channels. I’m joined by Rob Dwyer, Senior Technical Account Manager at Le...

Send us Fan Mail Your calendar says “1:1s,” but your brain hears “context switching.” Charlotte Ward sits down with Reagan Helms, VP of Customer Experience at Planning Center, to unpack a practical way AI can make us better managers: a management assistant that strengthens one-on-ones without turning leadership into autopilot. We get specific about how Reagan built his system and how it evolved, f...

Send us Fan Mail A lot has changed since the start of the year and not just job titles and cities. Charlotte Ward sits down with returning guest Alec Maloney to take stock of what is actually happening inside modern customer support teams as AI, automation, and faster tooling collide with the day-to-day reality of customers, tickets, and people management. We get practical about the new build vs b...

Send us Fan Mail AI can generate a clean looking knowledge article in seconds, but that speed comes with a trap: it makes bad knowledge easier to publish and easier to surface. Leslie O’Flahavan joins me to unpack a simple claim with big consequences for customer support leaders and knowledge management teams: AI won’t fix your knowledge quality problem, it will expose it. We get practical about w...

Send us Fan Mail The office can be a productivity killer or a leadership advantage, and the difference usually comes down to one thing: whether we design the day or let the day design us. I’m joined by Andrew Rios to get real about returning to the office after years of remote work, and what it takes to make that shift sustainable for customer support leaders running busy teams. We dig into the pr...

Send us Fan Mail AI in customer support gets reduced to one tired idea: ship a chatbot and cut tickets. That mindset misses where the real leverage is. We sit down with Robert Cabral, Head of Customer Experience at Runway, to talk about “AI beyond the queue” and what it looks like when an AI-first company uses automation to scale service while protecting the customer relationship. We get practical...

Send us Fan Mail Getting laid off can scramble more than your finances. It can shake your identity, your confidence, and the story you’ve been told about what “success” in customer support leadership is supposed to look like. That’s why this conversation with Jenny Dempsey hit so hard: she went from a clear leadership path in customer experience to two years of uncertainty, experimenting with cons...

Send us Fan Mail Customers are talking about you where your VOC program rarely looks and it’s shaping revenue, retention, and trust. Nate Brown joins me to introduce Fearless CX, a bold and practical way to lead customer experience in a time when fear is high, teams are tempted to retreat into silos, and “insular thinking” makes cross-functional work painfully slow. We dig into what Fearless CX lo...